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  Under effective stirring, a suspension of reduced iron powder (50 mmol) in 80 mL of ethanol was added to concentrated hydrochloric acid (5 mmol), heated at 65 °C for 0.5 h, and then cooled to 55–60 °C over 10 min. Then, 8 mL of 25% ammonium chloride aqueous solution was added. Substituted 4-bromo-nitronaphthalene (10 mmol) was added in portions (exothermic) while maintaining the internal temperature at 65–80 °C. The mixture was stirred at 55–65 °C for another 1–3 h and cooled to 40 °C. Diatomaceous earth was added, and the mixture was filtered through a diatomaceous earth mat. The filter cake was washed with dichloromethane (20 mL), and the liquid phase was extracted with dichloromethane. The organic phase was dried over sodium sulfate and concentrated under reduced pressure to obtain the desired 4-bromo-1-naphthylamine.;

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